On Feb. 20, 1992, more American homes tuned into The Simpsons than they did The Cosby Show or the Winter Olympics from Albertville, France. A foul-mouthed cartoon on a fourth-place network bested the Huxtables and the world's best amateur athletes. Fox over NBC and CBS—its first-ever victory in prime time. New over old.

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Why the shift? Well, the Olympic programming that night featured no marquee events, and Cosby was just two months away from ending its eight-season run. Meanwhile, The Simpsons, airing just its 52nd episode out of 500 (and counting), had put forth its most ambitious effort to date, an episode called "Homer at the Bat." Months of work went into corralling nine baseball players, a cross-section of young stars and established veterans, to guest-star as members of a rec-league softball team.

Sam Simon, the co-creator of The Simpsons, originally pitched the idea, and it was put into words by John Swartzwelder, a charter member of the show's writing staff, who would eventually pen 59 episodes, more than anyone else. On a staff full of fantasy baseball junkies, Swartzwelder was the über-geek, a fanatic who had rented out stadiums for hours at a time so he and his close friends could play ball. (Years after Swartzwelder's departure from the show, it's easy to see his influence endures. During the episode's roundtable DVD commentary, the word "Swartzweldian" is used with a deference and awe usually reserved for long-dead Nobel Laureates.)

If you're somehow unfamiliar with the episode, the premise was relatively simple: Mr. Burns's company softball team, having lost 28 of 30 games the previous season, goes on an incredible run when Homer starts hitting, well, homers with his WonderBat, carved from the fallen branch of a lightning-struck tree. (Sound familiar?) As the season winds down, it becomes a two-team race for the pennant: Springfield vs. Shelbyville. While dining at the Millionaires' Club with the owner of the Shelbyville Power Plant, a cocky Burns agrees to a handshake bet worth (you guessed it) $1 million.

To fix the game and secure his victory, Burns orders Smithers to enlist ballplayers like Cap Anson, Honus Wagner, and Jim Creighton. (Swartzwelder's choice of Creighton was particularly inspired. The ace pitcher for the Brooklyn Excelsiors in the 1850s and '60s, Creighton supposedly didn't strike out once while batting during the 20 games of the 1860 season. Creighton died two years later. He was 21.) Upon learning that his entire suggested lineup is dead, Burns instructs Smithers to come back with real ballplayers. And so he sets off across the country: nabbing Jose Canseco at a card convention, accosting a Graceland-touring Ozzie Smith, nearly getting shot in the woods by Mike Scioscia, and stopping by Don Mattingly's pink suburban house to interrupt his dish-washing.

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Before "Homer at the Bat," The Simpsons had used guest stars only sporadically—and never more than four of them in a single show, that I can remember. Recognizable voices popped up now and then, but no athlete had appeared until Magic Johnson on Oct. 17, 1991, five episodes into the third season. (Exactly three weeks later, Johnson held a press conference to announce he was HIV-positive and would immediately retire from the NBA.)

Now it was using nine guests, some of whom were obvious baseball Hall of Famers. The end result was not only an iconic piece of pop culture but a loving satire of baseball that looks downright prescient today, here on the other side of the Mitchell Report. Our heroes got drunk in bars, ingested odd substances because they were told to, and mindlessly clucked like diseased poultry. "Homer at the Bat" felt vaguely forbidden, like an animated addendum to Ball Four. This was the side of the sport we never saw.

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We couldn't pull our eyes away then. We still can't.

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Despite all the planning and prep, "Homer at the Bat" wasn't easy to put together. Of the players with guest-starring roles, only the Dodgers' Darryl Strawberry and Mike Scioscia were local. The script was pretty much locked down by summer 1991, but the writers and producers had to wait throughout the season for players to swing through Los Angeles to play the Dodgers or the California Angels so they could record their lines.

Aside from the Yankees' twofer of Don Mattingly and Steve Sax, each athlete coming to the Fox studios was booked for a single voiceover session, which often got cramped when friends and family tagged along. Ken Griffey Jr., then 21 and easing into his third season in the majors, showed up in early August with his father and Mariners teammate, who was a few months from retirement. (In the show's DVD commentary, showrunner Mike Reiss recalls Griffey Jr. laboring through his lines and getting increasingly upset. He "looked like he was going to beat the crap out of me," Reiss says.)

St. Louis Cardinals shortstop Ozzie Smith stopped by in early September with his Bart-impersonating son Nikko, who himself wound up on Fox television 14 years later as an American Idol finalist. "I knew he was a Simpsons fan and had the Bart thing down pretty good," Smith told me, "but I didn't know he could do anything like that." Smith also made sure to work through his script beforehand, unlike his peeved centerfielder. "I worked on those lines, even though there wasn't really a whole lot of them," he says. "I just wanted to get the inflections in the right place."

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Steve Sax, who retired three years after "Homer at the Bat" and did time as a financial adviser before becoming a life coach and motivational speaker, acknowledges a sizable debt to the show. (The writing staff's early preference for second base was Chicago's Ryne Sandberg.) "Sometimes, fans would yell, 'Hey, how's Homer?'" Sax told me. "I know they weren't talking about me hitting home runs, but it was a lot better than the stuff I used to hear."

Before The Simpsons, Sax was best known for a much-publicized case of the fielding yips that had dogged him throughout the '80s. His brief TV fame seemed to remove that period of his 14-year career from fans' minds. "Today, I still get people that ask me, 'What was it like to be on The Simpsons?' not, 'What was it like to face Nolan Ryan?'" (Actually, it's a legit question. Sax hit .265 lifetime against the Express. In their first matchup in April 1982, the rookie went 2-for-4 with a RBI triple. So, please, the next time you pass Steve Sax on the streets of Sacramento, ask him about Nolan Ryan.)

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Sax's affability at the recording session also stuck with some members of the staff, with one later admitting (half-jokingly, maybe) that the "closest I ever came to falling in love with a man was Steve Sax. He was so handsome, so sweet."

Showrunner Al Jean has said the players who committed were more than happy to do the show. Well, almost of all of them. "They were all really nice," Jean said on the DVD commentary, "except for one whose name rhymes with Manseco."

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Aside from the logistics of recording nine separate guest roles, plot lines had to be rewritten on the fly. Jose Canseco's scene originally called for him and Mrs. Krabappel to engage in Bull Durham-inspired extramarital shenanigans. Canseco's wife rejected the scene, and the staff had to do a last-minute Saturday afternoon rewrite when Oakland came south on a mid-August road trip.

Instead of Lothario, Canseco got to play hero, rushing into a woman's burning house to rescue her baby, then cat, followed by a player piano, washer, dryer, couch and recliner combo, high chair, TV, rug, kitchen table and chairs, lamp, and grandfather clock. Requesting the new sequence turned out to be the wiser move. Canseco and his wife had nearly divorced earlier that year before reconciling, and a week before "Homer at the Bat" aired, Canseco was arrested by Miami police for chasing down and ramming his wife's BMW twice with his red Porsche at 4:30 a.m. After the chase ended, he allegedly got out of his car, came over to his wife's driver-side window, and spit on it.

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The Don Mattingly of "Homer at the Bat" hit even closer to the mark. In August 1991, Yankees management ordered the team captain to cut his hair shorter. He refused, was benched by manager Stump Merrill, and fined $250, including $100 for every subsequent day that he didn't cut his hair. "I'm overwhelmed by the pettiness of it," Mattingly told reporters. "To me, long hair is down my back, touching my collar. I don't feel my hair is messy."

Six months later, when "Homer at the Bat" aired, Mattingly's storyline centered around Mr. Burns's insane interpretation of his first baseman's "sideburns." Mattingly is booted from the team, muttering as he walks away, "I still like him better than Steinbrenner."

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Most fans assumed that the show had cribbed from real-life events. In fact, Mr. Burns's sociopathic infatuation with sideburns was inspired by showrunner Al Jean's grandfather, who owned a hardware store in the '70s and would constantly berate his employees for their excessive follicular growth. Mattingly had recorded his dialogue a full month before his dustup with the Yankees.

Wade Boggs, who would labor through the worst year of his Hall of Fame career in 1992, was supposed to engage in a belching contest with Barney. As a player, Boggs was known for (among other pursuits) indulging in a bit o' drink from time to time; lore has it that he once drank dozens of beers during a team flight. Boggs tried to play down the story during a 2005 appearance on Pardon the Interruption—"It was a few Miller Lites," he claimed—but his occasional forays into boozy karaoke give the legend at least a little plausibility. For reasons now lost to history, the belching contest was scrapped in favor of a beer-fueled argument over who was England's greatest prime minister.

Still, rewriting plot lines was simple compared with getting the look of the players correct. The show's artists had never before had to tackle such a wide range of new faces on their animation cels. The show's biggest guest star to that point, Michael Jackson, posed no such challenge, as he voiced a morbidly obese white man. Matt Groening later said that "caricaturing real, living people" was the toughest challenge at the time, but they pulled it off, nailing features like Clemens's frat-boy spike, Strawberry's kiss-ass grin, and Canseco's chemistry-experiment-gone-wrong physique.

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Beyond these aesthetic and creative challenges, The Simpsons were in the midst of fighting off a ginned-up national outrage over the show. A backlash was on. Retailers became saturated with growing piles of Simpsons merchandise, and some licensing deals were abruptly dropped. Elementary schools from Ohio to Orange County started banning Bart Simpson T-shirts that had been deemed offensive. The show even became a point of contention during the 1992 presidential election. George H.W. Bush, struggling to boost his bona fides with conservatives, took the stage at the annual convention of National Religious Broadcasters on Jan. 27, three weeks before "Homer at the Bat" aired.

Bush ran through the usual Republican talking points, emphasizing "sanctity of life," working hard, sacrifice, and so forth. He then pivoted and started hammering nameless folks who would promote injustice and incivility.

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"I speak of decency, the moral courage to say what is right and condemn what is wrong," Bush said. "And we need a nation closer to The Waltons than The Simpsons." The partisan crowd inside the Sheraton Washington Hotel roared with laughter, but it was priceless publicity that put the show square in the national conversation.

Bush, meanwhile, repeated the shot in August at the Republican National Convention. This time, it backfired. Though the next scheduled episode was a repeat, the Simpsons staff cobbled together a new show open in just three days. In it, the family gathers around the TV to watch Bush's address, and Bart wryly observes how they're just like the Waltons: "We're praying for an end to the Depression, too."

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Bush really should've picked his battles more carefully. His wife was criticized in 1990 for calling the show "the dumbest thing I had ever seen." In return, "Marge Simpson" wrote her a letter in reply, explaining how she was deeply hurt by the comments. The situation was put to rest with the First Lady, amazingly, writing a letter back to the fictional TV mom, apologizing for her "loose tongue." It's hard to fathom now, two decades later, with the show ensconced in a family-hour time slot, but The Simpsons was once dangerous.

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"Homer at the Bat" was not remotely close to what you might consider a typical Simpsons episode. You have Chief Wiggum (sounding more like a Edward G. Robinson rip-off than a fully formed character) acting responsibly, ordering his team to stop shooting in the air in post-home run celebration. Ralph, of all people, outwits Bart at picking players for sandlot baseball. Lisa, normally so moralistic and holier-than-thou, taunts Darryl Strawberry and brings him to tears. These weren't the conventional character patterns that had worked so well, and one could see why cast members Harry Shearer and Julie Kavner openly hated Swartzwelder's script.

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Then there's the title of the episode, borrowed from "Casey at the Bat," the titular character being the ultimate symbol of baseball failure. In the end, Homer wins his team the pennant, albeit through inexplicable and unconventional means. But to see Homer excelling at anything flies in the face of the standard Simpsons script. In 22 minutes, he morphs from underdog to hero, and the contrast with the character we know from the rest of the series is more unnerving than welcome. The show was about inverting TV tropes. Homer's ineptitude was as vital to the show as Fred MacMurray's pipe was to My Three Sons. So when Homer smacks a bottom-of-the-ninth grand slam with his team down three runs, how the hell are we supposed to process that? Homer doesn't fail miserably; Bart doesn't quip his way out of trouble; Lisa doesn't roll her eyes in judgment. It was like watching some avant-garde, one-night-only experiment in ad hoc television.

Ratings might have had a little to do with that. Chasing Cosby was a priority for the Fox suits, and a splashy ensemble of ballplayers was likely to bring in big numbers. If the show had to tweak its own formula a little to do so, it was still young enough that it wouldn't look desperate; there were no sharks to jump, at that point. Die-hards might cringe a little, but in retrospect the episode looks a lot like a well-timed, what-the-hell swing for the fences.

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And for all the "very special episode" feel of "Homer at the Bat," it certainly doesn't go easy on its targets. This wasn't Mel Allen doing bloopers on This Week in Baseball. Nor was this the game "designed to break your heart." This was a far more bemused look at the putative national pastime. Coaches' inspirational talk is often clichéd gibberish? You bet. Ballplayers sometimes drink too much and get into barroom trouble? Hell yeah, they do. Acute radiation poisoning, cranial gigantism, and pits of eternal darkness? Meet your 2011 Red Sox. And because there were actual, living ballplayers in the show, every manic twist carried the added fillip that we were looking in on something we weren't supposed to see, something funny and unauthorized. This was Ball Four's demented stepson.

When the show aired in 1992, baseball was on the verge of a remarkable transformation. You could see hints of it in "Homer at the Bat." There is a meta-commentary on rising player salaries—Canseco's $50,000 game check to play softball would've been a raise, not a pay cut, as he claimed. Two years earlier, remember, the last of owner collusion cases had been settled, setting the stage for the 1994 strike. Two of the Springfield Nine, Canseco and Clemens, would be closely associated with PED use in years to come.

And maybe there's even a whiff of the jock-nerd culture war that would overtake baseball a decade later. With the bases loaded and the score tied 43-43 in the bottom of the ninth, Mr. Burns benches Strawberry, who has hit nine home runs in the game to this point. Burns explains to his increasingly incredulous star—and viewers at home, by extension—that he's pulling him for a right-handed batter, since a left-handed pitcher is on the mound. (Never mind that the Shelbyville pitcher is clearly shown holding the ball in his right hand just seconds before.) "It's called playing the percentages," Burns explains. "It's what smart managers do to win ballgames." The joke would come full circle in 2010, when the patron saint of sabermetrics, Bill James, appeared on a Moneyball-inspired episode and exuberantly took credit for making baseball "as much fun as doing your taxes."

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"Homer at the Bat" was proof you could see baseball in all its silliness and still love the game. Even the stars who were both target and participant in the spoof remember the episode fondly. Ozzie Smith is generally regarded as the greatest defensive shortstop in baseball history. He has played in three World Series, and he's earned election to the Hall of Fame—and yet he still gets questions from fans about The Simpsons whenever he does a card show or some other event. He can't escape it, but with no hesitation, he reckons his tumble into the Springfield Mystery Spot to be one of the highlights of his career.

"It ranks right up there, and people are still talking about it today," Smith says. "The Simpsons are a part of Americana, so to be part of an episode that featured all of those ballplayers from a special time? I guess it'll go down in history."

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Erik Malinowski, a freelance writer based in the Bay Area, is the former sports editor of Wired.com and a regular contributor to Wired magazine.